JPS6236369A - Benzoylurea compound - Google Patents

Abstract

NEW MATERIAL:A benzoylurea compound shown by the formula I or formula II(X1 and X2 are halogen; Y1 and Y2 are H, alkyl, chloroalkyl, phenyl which may contain substituent group, further Y1 is CF3; Z is H or NO2; both Y1 and Y2 may form benzene ring). EXAMPLE:N-(4-Methyl-2-thiazoyl)-N'-2,6-dichlorobenzoylurea. USE:Particularly useful as an insecticide. PREPARATION:A compound shown by the formula III or formula IV is reacted with a compound shown by the formula V in a solvent such as N,N- dimethylformamide, dimethyl sulfoxide, benzene, toluene, 1,2-dichloroethane or ethyl acetate at 0-80 deg.C, preferably 0 deg.C - room temperature for 2-20hr to give a compound shown by the formula I or formula II.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a benzoyl urea compound and an insecticide containing the benzoyl urea compound as an active ingredient.

Specifically, the general formula (wherein, Xl represents a halogen atom, Yl represents hydrogen, an alkyl group, a chloroalkyl group, a trifluoromethyl group, or a phenyl group which may have a substituent, and Z represents hydrogen or a nitro group) In addition, Yl may form a benzene ring with Z.) or the general formula (wherein, Xl and X2 represent a halogen atom, and Y2 has hydrogen, an alkyl group, a chloroalkyl group, or a substituent. It particularly relates to a benzoyl urea compound represented by a phenyl group, Z represents hydrogen or a nitro group, and Y2 may form a benzene ring together with Z.

The present invention further relates to an insecticide containing a benzoyl urea compound represented by the above general formulas (1) and (2) as an active ingredient.

In the general formula I and general formula (II), X and X represent halogen atoms, and such halogen atoms include chlorine,
Fluorine, bromine or iodine.

Yl represents hydrogen, an alkyl group, a chloroalkyl group, a nitrifluoromethyl group, or a phenyl group which may have a substituent, and the alkyl group is a linear or branched alkyl group having 1 to 10 carbon atoms. It is the basis. The chloroalkyl group is a chloroalkyl group having 1 to 10 carbon atoms. IE
Examples of substituents in the phenyl group which may have substituents include a halogen atom, an alkoxyl group having 1 to 10 carbon atoms, or a nitro group.

Y indicates hydrogen, an alkyl group, a chloroalkyl group, or a phenyl group which may have a substituent, and examples of such alkyl groups include monochloro, which is a linear or branched alkyl group having 1 to 10 carbon atoms. The alkyl group is a chloroalkyl group having 1 to 10 carbon atoms. Substituents in the phenyl group which may have a W substituent include a halogen atom, a carbon number of 1 to
10 alkoxyl group or nitro group.

Yl or Y2 may form a benzene ring together with Z.

Compounds of the invention may be used, for example. Compound represented by the following general formula (In the formula, X is the same as above) and a compound represented by the following general formula (In the formula, Yl and 2 are the same as above) It is obtained by reacting with.

Alternatively, it can be obtained by reacting a compound represented by the following general formula (wherein Xl and Xs are the same as above) with a compound represented by the following general formula (wherein Y2 and Z are the same as above).

In the above method, reaction solvents such as N,N-dimethylformamide, dimethylsulfoxide, benzene, toluene, 1,2-dichloroethane or ethyl acetate are generally used.

The reaction temperature is 0 to 80°C, preferably 0 to room temperature.
Allow to react for 20 hours.

The compounds of the present invention exhibit excellent insecticidal activity. It has a particularly insecticidal effect.

Insects targeted include paddy rice pests: Japanese rice beetle, rice beetle, brown weevil, and upland crop pests: Japanese armyworm, mealybug, armyworm,
Green leaf beetles Tea pests: Tea leafhoppers, Japanese teal fruit tree pests: Red leafhoppers, Japanese peach beetles Sanitary pests: Effective against American cockroaches, Culex mosquitoes, houseflies, termites, etc.

In use, generally Q, 1ppm = 10°000
pp rn, preferably 0.5 pp pm-2,0
It is carried out at an active ingredient concentration of 00 p Il m.

When the compound of the present invention is used as an active ingredient of an insecticide, it is preferable to formulate it in the form of an emulsion, a powder, an aqueous agent, a liquid, etc., and these preparations can be used as they are or with the addition of a diluent. can be used.

To formulate the above formulation, use talc and kaolin.

bentonite, silica, white carbon, clay,
Solid carrier such as yQ powder, water, diluent such as xylene, toluene, dimethyl sulfoxide, alcohol, emulsifier 5
Examples include dispersants and spreading agents.

In addition, it can be used in combination with other agricultural chemicals such as insecticides, acaricides, fungicides, growth regulators, etc.

Example IN-(4-methyl-2-thiazoyl)-N'-
2,5-dichlorobenzoyl urea dry ethyl acetate 2mQ
343 mg of 2-amino-4-methylthiazole was dissolved in the solution, and then a solution of 648 mg of 2,6-cyclopenzoyl isocyanate in 3 mQ of dry ethyl acetate was added dropwise with stirring at room temperature.

After stirring for 4 hours and completing the reaction, ethyl acetate was distilled off under reduced pressure, and diethyl ether was added to precipitate crystals. The crystals are filtered off with suction and then dried.

N-(4-methyl-2-thiazoyl) -N'-2,6
-Dichlorobenzoyl urea 891 mg (yield 90%) is obtained. Melting point 247°C, Example 2N-(5-
Nitro-2-thiazoyl)-N'-2,6-dichlorobenzoyl urea dry N,N-dimethylformamide 2mQ
Dissolve 218 mg of 2-amino-5-nitrothiazole in and add 3 mQ of dry ethyl acetate.

Then, a solution of 324 mg of 2,6-dichlorobenzoyl isocyanate in 3 mQ of dry ethyl acetate was added dropwise at room temperature while stirring.

After stirring for 4 hours and completing the reaction, ethyl acetate was distilled off under reduced pressure, and the mixture was poured into about 50 mfi of water to precipitate crystals.

The crystals are filtered off with suction and then dried.

N-(5-nitro-2-thiazoyl)-N'-2,6-
530 mg (yield 98%) of dichlorobenzoyl urea are obtained. Melting point: 215°C.

Example 3 Dissolve 252 mg of 2-amino-4-trifluoromethylthiazole in 5 m Q of 3-(4-)-lifluoromethylthiazol-2-yl)-1-(2-bromobenzoyl) dry ethyl acetate. death.

Then, 339 mg of 0-brombenzoyl isocyanate was added dropwise while stirring at room temperature.

After stirring for 5 hours and completing the reaction, ethyl acetate was distilled off under reduced pressure, and diethyl ether was added to precipitate crystals. The crystals are filtered off under suction and then dried.

560 mg of 3-(4-)-lifluoromethylthiazol-2-yl)-1-(2-bromobenzoyl)urea
(Yield 95%) is obtained. Melting point: 203-208°C.

Various benzoyl urea compounds can be obtained in the same manner.

The melting points of each compound are shown in Tables 1 and 2.

Formulation Example I N-(4-methyl-2-thiazoyl) -N'-2゜6
-Dichlorobenzoyl urea 10 parts talc
Mix 90 parts;
Use as a powder.

Formulation Example 2 3-(4-trifluoromethylthiazol-2-yl)
-10 parts of 1-(2-bromobenzoyl)urea 70 parts of N,N,-dimethylformamide 20 parts of polyoxyethylene alkylphenyl ether are uniformly mixed and dissolved to prepare an emulsion.

Test Example 1 Test method for diamondback moth: After preparing an emulsion of the compound of the present invention at a predetermined concentration (15.6 ppm), cabbage leaves were immersed for 20 seconds, air-dried, and 3rd instar larvae were tested in triplicate with 10 heads per group. were inoculated and raised at 25°C. The mortality rate of 88 eyes after drug treatment was determined.

The results are shown in Table 3.

Table 3■ Test example 2 Examination method for Chanokokakumonhamaki:
A predetermined concentration (500 ppm) of the compound of the present invention in artificial feed
After mixing and preparing the mixture, it was fed to Chanokakumonhamaki larvae and reared at 25°C, and the mortality rate on the 20th day was determined.

The results are shown in Table 4.

Table 4 In these tests, the following substances were used as comparative compounds. All comparative compounds are from U.S. Patent No. 4. '164
, No. 581.

Comparative compound b

Claims (4)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1 represents a halogen atom, Y_1 represents hydrogen,
It represents an alkyl group, a chloroalkyl group, a trifluoromethyl group, or a phenyl group which may have a substituent, and Z represents hydrogen or a nitro group. Further, Y_1 may form a benzene ring together with Z. ) A benzoyl urea compound represented by (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1 and X_2 represent halogen atoms, Y_
2 represents hydrogen, an alkyl group, a chloroalkyl group, or a phenyl group which may have a substituent, and Z represents hydrogen or a nitro group. Further, Y_2 may form a benzene ring together with Z. ) A benzoyl urea compound represented by (3) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X_1 represents a halogen atom, Y_1 represents hydrogen,
It represents an alkyl group, a chloroalkyl group, a trifluoromethyl group, or a phenyl group which may have a substituent, and Z represents hydrogen or a nitro group. Further, Y_1 may form a benzene ring together with Z. ) An insecticide whose active ingredient is a benzoyl urea compound. (4) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X_1 and X_2 represent halogen atoms, and Y_
2 represents hydrogen, an alkyl group, a chloroalkyl group, or a phenyl group which may have a substituent, and Z represents hydrogen or a nitro group. Further, Y_2 may form a benzene ring together with Z. ) An insecticide whose active ingredient is a benzoyl urea compound.